Potassium Hydroxide → HCID 9939669、化合物

HRID 1954276ノート

反応式

HRID 1954276 の反応式
C[O:2][C:3]([C:5]1[C:9]([O:10][CH3:11])=[C:8]([S:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:34]4[C:33]([CH3:35])=[C:32]([CH3:36])[S:31][C:30]=4[C:29]([Br:37])=[C:28]4[C:23]=3[CH:24]=[CH:25][CH:26]=[CH:27]4)=[CH:18][C:17]=2[CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)(=[O:14])=[O:13])[S:7][CH:6]=1)=[O:4].[OH-].[K+]>C1COCC1.CO>[Br:37][C:29]1[C:30]2[S:31][C:32]([CH3:36])=[C:33]([CH3:35])[C:34]=2[C:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][S:12]([C:8]3[S:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:9]=3[O:10][CH3:11])(=[O:14])=[O:13])=[C:17]([CH:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[CH:18]=2)=[C:23]2[C:28]=1[CH:27]=[CH:26][CH:25]=[CH:24]2

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 54249985HCID 54249985、化合物

生成物 1

HCID 9939669HCID 9939669、化合物収率 85%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

At ambient temperature, to a stirred solution of 5-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid methyl ester (0.722 g, 1.05 mmol) in THF:MeOH (3:2, 10 mL) was added 1N KOH (5.26 mL). After 1.5 h, the reaction was quenched with 1N HCl (40 mL) and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated. Purification on 2% H3PO4 /MeOH treated Biotage KP-Sil, eluting with 25% EtOAc/hexane gave 0.596 g (85%) of the title compound as a white solid, mp >225° C.; 1H NMR (DMSO-d6) δ 1.34-1.39 (m, 2 H), 1.49-1.54 (m, 5 H), 1.62-1.73 (m, 3 H), 1.79-1.83 (m, 1 H), 2.43 (s, 3 H), 3.23 (quintet, 1 H), 3.97 (s, 3 H), 7.24 (dd, 1 H), 7.30 (d, 1 H), 7.34-7.36 (m, 2 H), 7.49 (t, 1 H), 7.64 (t, 1 H), 8.19 (d, 1 H), 8.72 (s, 1 H), 13.34 (br. s, 1 H). IR (KBr) 3400, 2950, 1690, 1375 and 860 cm-1. mass spectrum (-ESI), m/z 669/671 (M-H). Anal. Calcd. for C31H27BrO6S3 : C, 55.44; H, 4.05 N, 0.00. Found: C, 55.25; H, 4.11 N, 0.01.

後処理

  1. customthe reaction was quenched with 1N HCl (40 mL)
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification on 2% H3PO4 /MeOH treated Biotage KP-Sil
  6. washeluting with 25% EtOAc/hexane

出典と根拠

ORDレコード
ord-0fe03e3810584fe78deff384ef045ac1
出典データセット
uspto-grants-2000_09
特許番号
US06121271

反応ノート

読み込み中…